Aniline derivatives having herbicidal activity, their preparation and their use

- Sankyo Company, Limited

Compounds of formula (I): ##STR1## (wherein: R.sup.1 is optionally substituted alkyl, cycloalkyl, optionally substituted alkoxy, or optionally substituted alkylthio; R.sup.2 is hydrogen, optionally substituted alkyl, cycloalkyl, optionally substituted alkenyl, optionally substituted alkynyl or a group of formula --YR.sup.7 ; R.sup.3 is optionally substituted alkyl, cycloalkyl, optionally substituted alkoxy group, optionally substituted alkenyl, optionally substituted alkynyl, halogen, nitro or a group of formula --COR.sup.8, wherein R.sup.8 is hydrogen, alkyl, cycloalkyl or alkoxy; R.sup.4 and R.sup.5 are each hydrogen atom or alkyl; R.sup.6 is optionally substituted alkyl, cycloalkyl, optionally substituted alkoxy group, optionally substituted alkenyl, optionally substituted alkynyl, halogen, nitro, or a group of formula --COR.sup.8, as defined above;A, Q and X are each oxygen or sulfur; Y is a group of formula --CO--, --COO--, --CH.sub.2 O--, --CH.sub.2 S--, --CH.sub.2 CH.sub.2 O--, --CH.sub.2 CH.sub.2 S--, --CH.sub.2 CO--, --CH.sub.2 COO--, --CH(Me)COO--, --CH.sub.2 CH.sub.2 CO--, --CH.sub.2 OCO--, CH.sub.2 OCOO-- and --CH.sub.2 CH.sub.2 OCO--; R.sup.7 is optionally substituted alkyl group, cycloalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted aralkyl, or an optionally substituted heterocycle; and m and n are each an integer from 0 to 4; and herbicidally acceptable addition salts thereof) are useful as herbicides.

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Claims

1. A compound of formula (I): ##STR18## wherein: R.sup.1 represents:

an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
a cycloalkyl group having from 3 to 6 carbon atoms;
an alkoxy group having from 1 to 6 carbon atoms, said alkoxy group being unsubstituted or being substituted by from 1 to 4 halogen atoms; or
an alkylthio group having from 1 to 6 carbon atoms, said alkylthio group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
R.sup.2 represents:
a hydrogen atom;
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by a hydroxy group or by from 1 to 4 halogen atoms;
a cycloalkyl group having from 3 to 6 carbon atoms;
an alkenyl group having from 2 to 6 carbon atoms, said alkenyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
an alkynyl group having from 2 to 6 carbon atoms, said alkynyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms; or
a group represented by the formula --YR.sup.7;
R.sup.3 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
a cycloalkyl group having from 3 to 6 carbon atoms;
an alkoxy group having from 1 to 6 carbon atoms, said alkoxy group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
an alkenyl group having from 2 to 6 carbon atoms, said alkenyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
an alkynyl group having from 2 to 6 carbon atoms, said alkynyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
a halogen atom;
a nitro group; or
a group of formula --COR.sup.8, wherein R.sup.8 represents a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms, a cycloalkyl group having from 3 to 6 carbon atoms or an alkoxy group having from 1 to 6 carbon atoms;
R.sup.4 and R.sup.5 are the same or different and each represents a hydrogen atom or an alkyl group having from 1 to 6 carbon atoms;
R.sup.6 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
a cycloalkyl group having from 3 to 6 carbon atoms;
an alkoxy group having from 1 to 6 carbon atoms, said alkoxy group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
an alkenyl group having from 2 to 6 carbon atoms, said alkenyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms,
an alkynyl group having from 2 to 6 carbon atoms, said alkynyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
a halogen atom;
a nitro group; or
a group of formula --COR.sup.8, wherein R.sup.8 represents a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms, a cycloalkyl group having from 3 to 6 carbon atoms or an alkoxy group having from 1 to 6 carbon atoms;
A represents an oxygen atom or a sulfur atom;
X represents an oxygen atom or a sulfur atom;
Y represents a group selected from the group consisting of the groups of formulae --CO--, --COO--, --CH.sub.2 O--, --CH.sub.2 S--, --CH.sub.2 CH.sub.2 O--, --CH.sub.2 CH.sub.2 S--, --CH.sub.2 CO--, --CH.sub.2 COO--, --CH(Me)COO--, --CH.sub.2 CH.sub.2 CO--, --CH.sub.2 OCO--, CH.sub.2 OCOO-- and --CH.sub.2 CH.sub.2 OCO--;
R.sup.7 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 6 carbon atoms, an alkylthio group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
a cycloalkyl group having from 3 to 6 carbon atoms;
an alkenyl group having from 2 to 6 carbon atoms, said alkenyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
an alkynyl group having from 2 to 6 carbon atoms, said alkynyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
a carbocyclic aryl group having from 6 to 14 ring carbon atoms, said aryl group being unsubstituted or being substituted by at least one substituent selected from the group consisting of alkyl groups having from 1 to 6 carbon atoms, alkoxy groups having from 1 to 6 carbon atoms and halogen atoms;
an aralkyl group wherein the aryl moiety is a carbocyclic aryl group having from 6 to 10 ring carbon atoms which is unsubstituted or is substituted by from 1 to 4 halogen atoms, and the alkyl moiety has from 1 to 6 carbon atoms; or
a heterocyclic group having from 4 to 10 ring atoms including at least one ring heteroatom selected from the group consisting of oxygen atoms, sulfur atoms and nitrogen atoms, said heterocyclic group being fully unsaturated, partly unsaturated or saturated and being either unsubstituted, substituted by at least one substituent selected from alkyl groups having from 1 to 6 carbon atoms, alkoxy groups having from 1 to 6 carbon atoms and halogen atoms, or fused with a carbocyclic aryl group having from 6 to 10 ring carbon atoms;
Q represents an oxygen atom or a sulfur atom;
m represents an integer from 0 to 4 and, where m is an integer from 2 to 4, each R.sup.6 may be the same or different; and
n represents an integer from 0 to 4 and, where n is an integer from 2 to 4, each R.sup.3 may be the same or different;
and herbicidally acceptable addition salts thereof.

2. The compound according to claim 1, wherein:

R.sup.1 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
a cycloalkyl group having from 3 to 6 carbon atoms; or
an alkoxy group having from 1 to 6 carbon atoms, said alkoxy group being unsubstituted or being substituted by from 1 to 4 halogen atoms.

3. The compound according to claim 1, wherein:

R.sup.1 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms; or
an unsubstituted alkoxy group having from 1 to 6 carbon atoms.

4. The compound according to claim 1, wherein:

R.sup.1 represents:
an alkyl group having from 1 to 3 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 3 carbon atoms; or
an unsubstituted alkoxy group having from 1 to 3 carbon atoms.

5. The compound according to claim 1, wherein R.sup.1 represents a methyl group or a methoxy group.

6. The compound according to claim 1, wherein R.sup.1 represents a methoxy group.

7. The compound according to claim 1, wherein:

R.sup.2 represents:
a hydrogen atom;
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by a hydroxy group or by from 1 to 4 halogen atoms;
a cycloalkyl group having from 3 to 6 carbon atoms; or
a group represented by the formula --YR.sup.7, as defined in claim 1.

8. The compound according to claim 1, wherein:

R.sup.2 represents:
a hydrogen atom;
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by a hydroxy group; or
a group represented by the formula --YR.sup.7, as defined in claim 1.

9. The compound according to claim 1, wherein:

R.sup.2 represents:
a hydrogen atom;
an alkyl group having from 1 to 3 carbon atoms which is substituted by a hydroxy group; or
a group represented by the formula --YR.sup.7, as defined in claim 1.

10. The compound according to claim 1, wherein R.sup.2 represents a hydrogen atom, a hydroxymethyl group or a group represented by the formula --YR.sup.7, as defined in claim 1.

11. The compound according to claim 1, wherein R.sup.2 represents a hydrogen atom.

12. The compound according to claim 1, wherein Y represents a group selected from the group consisting of the groups of formulae --CO--, --COO--, --CH.sub.2 O--, --CH.sub.2 CH.sub.2 O--, --CH.sub.2 CO--, --CH.sub.2 COO--, --CH.sub.2 CH.sub.2 CO--, --CH.sub.2 OCO--, --CH.sub.2 OCOO-- and --CH.sub.2 CH.sub.2 OCO--.

13. The compound according to claim 1, wherein Y represents a group selected from the group consisting of the groups of formulae --CO--, --COO--, --CH.sub.2 O--, --CH.sub.2 CH.sub.2 O--, --CH.sub.2 OCO-- and --CH.sub.2 OCOO--.

14. The compound according to claim 1, wherein Y represents a group selected from the group consisting of the groups of formulae --CO--, --COO--, --CH.sub.2 O--, --CH.sub.2 OCO-- and --CH.sub.2 OCOO--.

15. The compound according to claim 1, wherein Y represents a group selected from the group consisting of the groups of formulae --CO--, --COO-- and --CH.sub.2 OCO--.

16. The compound according to claim 1, wherein:

R.sup.7 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
a cycloalkyl group having from 3 to 6 carbon atoms;
an alkenyl group having from 2 to 6 carbon atoms, said alkenyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
an alkynyl group having from 2 to 6 carbon atoms, said alkynyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
a carbocyclic aryl group having from 6 to 14 ring carbon atoms, said aryl group being unsubstituted or being substituted by from 1 to 3 alkyl groups having from 1 to 6 carbon atoms, 1 to 3 alkoxy groups having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
an aralkyl group wherein the aryl moiety is a carbocyclic aryl group having from 6 to 14 ring carbon atoms, said aryl group being unsubstituted or being substituted by from 1 to 4 halogen atoms, and the alkyl moiety has from 1 to 6 carbon atoms; or
a heterocyclic group having from 4 to 10 ring atoms including at least one ring heteroatom selected from the group consisting of oxygen atoms, sulfur atoms and nitrogen atoms, said heterocyclic group being fully unsaturated, partly unsaturated or saturated and being either unsubstituted, substituted by at least one substituent selected from alkyl groups having from 1 to 6 carbon atoms, alkoxy groups having from 1 to 6 carbon atoms and halogen atoms, or fused with a carbocyclic aryl group having from 6 to 10 ring carbon atoms.

17. The compound according to claim 1, wherein R.sup.7 represents an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms.

18. The compound according to claim 1, wherein R.sup.7 represents an alkyl group having from 1 to 3 carbon atoms, said alkyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms.

19. The compound according to claim 1, wherein R.sup.7 represents an ethyl group or a 2,2,2-trichloroethyl group.

20. The compound according to claim 1, wherein:

R.sup.3 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by a alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
a cycloalkyl group having from 3 to 6 carbon atoms;
an alkoxy group having from 1 to 6 carbon atoms, said alkoxy group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
a halogen atom;
a nitro group; or
a group represented by the formula --COR.sup.8, as defined in claim 1.

21. The compound according to claim 1, wherein:

R.sup.3 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
an alkoxy group having from 1 to 6 carbon atoms, said alkoxy group being unsubstituted or being substituted by from 1 to 4 halogen atoms; or
a halogen atom.

22. The compound according to claim 1, wherein:

R.sup.3 represents:
an unsubstituted alkyl group having from 1 to 3 carbon atoms;
an alkoxy group having from 1 to 3 carbon atoms; or
a halogen atom.

23. The compound according to claim 1, wherein R.sup.3 represents a methyl group, an ethyl group, a methoxy group, an ethoxy group, a fluorine atom or a chlorine atom.

24. The compound according to claim 1, wherein R.sup.3 represents a methyl group.

25. The compound according to claim 1, wherein R.sup.4 and R.sup.5 are the same or different and each represents a hydrogen atom or a methyl group.

26. The compound according to claim 1, wherein R.sup.4 represents a hydrogen atom or a methyl group and R.sup.5 represents a hydrogen atom.

27. The compound according to claim 1, wherein R.sup.4 and R.sup.5 each represent a hydrogen atom.

28. The compound according to claim 1, wherein:

R.sup.6 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by a alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
a cycloalkyl group having from 3 to 6 carbon atoms;
an alkoxy group having from 1 to 6 carbon atoms, said alkoxy group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
a halogen atom; or
a group represented by the formula --COR.sup.8, as defined in claim 1.

29. The compound according to claim 1, wherein:

R.sup.6 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
an alkoxy group having from 1 to 6 carbon atoms, said alkoxy group being unsubstituted or being substituted by from 1 to 4 halogen atoms; or
a halogen atom.

30. The compound according to claim 1, wherein:

R.sup.6 represents:
an unsubstituted alkyl group having from 1 to 3 carbon atoms;
an unsubstituted alkoxy group having from 1 to 3 carbon atoms; or
a halogen atom.

31. The compound according to claim 1, wherein R.sup.6 represents a methoxy group, a fluorine atom or a chlorine atom.

32. The compound according to claim 1, wherein R.sup.6 represents a fluorine atom or a chlorine atom.

33. The compound according to claim 1, wherein R.sup.8 represents an alkyl group having from 1 to 3 carbon atoms or an alkoxy group having from 1 to 3 carbon atoms.

34. The compound according to claim 1, wherein R.sup.8 represents an alkoxy group having from 1 to 3 carbon atoms.

35. The compound according to claim 1, wherein R.sup.8 represents a methoxy group.

36. The compound according to claim 1, wherein A represents an oxygen atom.

37. The compound according to claim 1, wherein X represents an oxygen atom.

38. The compound according to claim 1, wherein Q represents a sulfur atom.

39. The compound according to claim 1, wherein m represents an integer from 0 to 3.

40. The compound according to claim 1, wherein m represents an integer of 0 or 1.

41. The compound according to claim 1, wherein m represents an integer of 0.

42. The compound according to claim 1, wherein n represents an integer from 0 to 3.

43. The compound according to claim 1, wherein n represents an integer from 0 to 2.

44. The compound according to claim 1, wherein n represents an integer of 0 or 1.

45. The compound according to claim 1, wherein n represents an integer of 1.

46. The compound according to claim 1 wherein:

R.sup.1 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
a cycloalkyl group having from 3 to 6 carbon atoms; or
an alkoxy group having from 1 to 6 carbon atoms, said alkoxy group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
R.sup.2 represents:
a hydrogen atom;
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by a hydroxy group or by from 1 to 4 halogen atoms;
a cycloalkyl group having from 3 to 6 carbon atoms; or
a group represented by the formula --YR.sup.7, wherein:
Y represents a group selected from the group consisting of the the groups of formulae --CO--, --COO--, --CH.sub.2 O--, --CH.sub.2 CH.sub.2 O--, --CH.sub.2 CO--, --CH.sub.2 COO--, --CH.sub.2 CH.sub.2 CO--, --CH.sub.2 OCO--, --CH.sub.2 OCOO-- and --CH.sub.2 CH.sub.2 OCO--, and
R.sup.7 represents an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms,
a cycloalkyl group having from 3 to 6 carbon atoms,
an alkenyl group having from 2 to 6 carbon atoms, said alkenyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms,
an alkynyl group having from 2 to 6 carbon atoms, said alkynyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms,
a carbocyclic aryl group having from 6 to 14 ring carbon atoms, said aryl group being unsubstituted or being substituted by from 1 to 3 alkyl groups having from 1 to 6 carbon atoms, 1 to 3 alkoxy groups having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms,
an aralkyl group wherein the aryl moiety is a carbocyclic aryl group having from 6 to 14 ring carbon atoms, said aryl group being unsubstituted or being substituted by from 1 to 4 halogen atoms, and the alkyl moiety has from 1 to 6 carbon atoms, or
a heterocyclic group having from 4 to 10 ring atoms including at least one ring heteroatom selected from the group consisting of oxygen atoms, sulfur atoms and nitrogen atoms, said heterocyclic group being fully unsaturated, partly unsaturated or saturated and being either unsubstituted, substituted by at least one substituent selected from alkyl groups having from 1 to 6 carbon atoms, alkoxy groups having from 1 to 6 carbon atoms and halogen atoms, or fused with a carbocyclic aryl group having from 6 to 10 ring carbon atoms;
R.sup.3 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by a alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
a cycloalkyl group having from 3 to 6 carbon atoms;
an alkoxy group having from 1 to 6 carbon atoms, said alkoxy group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
a halogen atom;
a nitro group; or
a group represented by the formula --COR.sup.8, wherein R.sup.8 represents an alkyl group having from 1 to 3 carbon atoms or an alkoxy group having from 1 to 3 carbon atoms;
R.sup.4 and R.sup.5 are the same or different and each represents a hydrogen atom or a methyl group;
R.sup.6 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by a alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
a cycloalkyl group having from 3 to 6 carbon atoms;
an alkoxy group having from 1 to 6 carbon atoms, said alkoxy group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
a halogen atom; or
a group represented by the formula --COR.sup.8, wherein R.sup.8 represents an alkyl group having from 1 to 3 carbon atoms or an alkoxy group having from 1 to 3 carbon atoms; and
m and n are the same or different and each represents an integer from 0 to 3.

47. The compound according to claim 1 wherein:

R.sup.1 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms; or
an unsubstituted alkoxy group having from 1 to 6 carbon atoms;
R.sup.2 represents:
a hydrogen atom;
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by a hydroxy group; or
a group represented by the formula --YR.sup.7, wherein Y represents a group selected from the group consisting of the groups of formulae --CO--, --COO--, --CH.sub.2 O--, --CH.sub.2 CH.sub.2 O--, --CH.sub.2 OCO-- and --CH.sub.2 OCOO-- and R.sup.7 represents an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
R.sup.3 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
an alkoxy group having from 1 to 6 carbon atoms, said alkoxy group being unsubstituted or being substituted by from 1 to 4 halogen atoms; or
a halogen atom;
R.sup.4 and R.sup.5 are the same or different and each represents a hydrogen atom or a methyl group;
R.sup.6 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
an alkoxy group having from 1 to 6 carbon atoms, said alkoxy group being unsubstituted or being substituted by from 1 to 4 halogen atoms; or
a halogen atom; and
m represents an integer from 0 to 3 and n represents an integer from 0 to 2.

48. The compound according to claim 1 wherein:

R.sup.1 represents:
an alkyl group having from 1 to 3 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 3 carbon atoms; or
an unsubstituted alkoxy group having from 1 to 3 carbon atoms;
R.sup.2 represents:
a hydrogen atom;
an alkyl group having from 1 to 3 carbon atoms which is substituted by a hydroxy group; or
a group represented by the formula --YR.sup.7, wherein Y represents a group selected from the group consisting of the groups of formulae --CO--, --COO--, --CH.sub.2 O--, --CH.sub.2 OCO-- and --CH.sub.2 OCOO-- and R.sup.7 represents an alkyl group having from 1 to 3 carbon atoms, said alkyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
R.sup.3 represents:
an unsubstituted alkyl group having from 1 to 3 carbon atoms;
an alkoxy group having from 1 to 3 carbon atoms; or
a halogen atom;
R.sup.4 represents a hydrogen atom or a methyl group and R.sup.5 represents a hydrogen atom;
R.sup.6 represents:
an unsubstituted alkyl group having from 1 to 3 carbon atoms;
an unsubstituted alkoxy group having from 1 to 3 carbon atoms; or
a halogen atom; and
m and n are the same or different and each represents an integer of 0 or 1.

49. The compound according to claim 1 wherein:

R.sup.1 represents a methyl group or a methoxy group;
R.sup.2 represents a hydrogen atom, a hydroxymethyl group or a group represented by the formula --YR.sup.7 wherein Y represents a group selected from the group consisting of the groups of formulae --CO--, --COO-- or --CH.sub.2 OCO-- and R.sup.7 represents an ethyl group or a 2,2,2-trichloroethyl group;
R.sup.3 represents a methyl group, an ethyl group, a methoxy group, an ethoxy group, a fluorine atom or a chlorine atom;
R.sup.4 represents a hydrogen atom or a methyl group and R.sup.5 represents a hydrogen atom;
R.sup.6 represents a methoxy group, a fluorine atom or a chlorine atom;
m and n are the same or different and each represents an integer of 0 or 1;
A represents an oxygen atom;
X represents an oxygen atom; and
Q represents a sulfur atom.

50. The compound according to claim 1 wherein:

R.sup.1 represents a methoxy group;
R.sup.2 represents a hydrogen atom;
R.sup.3 represents a methyl group;
R.sup.4 and R.sup.5 each represent a hydrogen atom;
m represents an integer of 0;
n represents an integer of 1;
A represents an oxygen atom;
X represents an oxygen atom; and
Q represents a sulfur atom.

51. The compound according to claim 1 wherein m represents an integer of 1 and R.sup.3 is at the 2-position of the phenyl ring.

52. The compound according to claim 1, wherein:

R.sup.x represents an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
R.sup.2 represents:
a hydrogen atom;
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
an alkenyl group having from 3 to 6 carbon atoms, said alkenyl group being unsubstituted;
an alkynyl group having from 3 to 6 carbon atoms, said alkynyl group being unsubstituted; or
an alkoxycarbonyl group wherein the alkoxy moiety has from 1 to 6 carbon atoms;
R.sup.3 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
an alkoxy group having from 1 to 6 carbon atoms, said alkoxy group being unsubstituted;
an alkenyl group having from 3 to 6 carbon atoms, said alkenyl group being unsubstituted;
an alkynyl group having from 3 to 6 carbon atoms, said alkynyl group being unsubstituted;
a halogen atom;
a nitro group; or
a formyl group;
R.sup.4 and R.sup.5 are the same or different and each represents a hydrogen atom or an alkyl group having from 1 to 6 carbon atoms;
R.sup.6 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
an alkoxy group having from 1 to 6 carbon atoms, said alkoxy group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
an alkenyl group having from 3 to 6 carbon atoms, said alkenyl group being unsubstituted;
an alkynyl group having from 3 to 6 carbon atoms, said alkynyl group being unsubstituted; or
a halogen atom;
A represents an oxygen atom or a sulfur atom;
X represents an oxygen atom;
Q represents a sulfur atom;
m represents an integer from 0 to 4 and, where m is an integer from 2 to 4, each R.sup.6 may be the same or different; and
n represents an integer from 0 to 4 and, where n is an integer from 2 to 4, each R.sup.3 may be the same or different;
and herbicidally acceptable addition salts thereof.

53. The compound according to claim 1, wherein:

R.sup.1 represents:
an alkoxy group having from 1 to 6 carbon atoms, said alkoxy group being unsubstituted or being substituted by from 1 to 4 halogen atoms; or
an alkylthio group having from 1 to 6 carbon atoms, said alkylthio group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
R.sup.2 represents:
a hydrogen atom; or
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
R.sup.3 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
an alkoxy group having from 1 to 6 carbon atoms, said alkoxy group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
a halogen atom;
a nitro group; or
a formyl group;
R.sup.4 and R.sup.5 are the same or different and each represents a hydrogen atom or an alkyl group having from 1 to 6 carbon atoms;
R.sup.6 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted
or being substituted by from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
an alkoxy group having from 1 to 6 carbon atoms, said alkoxy group being unsubstituted or being substituted by from 1 to 4 halogen atoms; or
a halogen atom;
A represents an oxygen atom or a sulfur atom;
X represents an oxygen atom or a sulfur atom;
Q represents an oxygen atom or a sulfur atom;
m represents an integer from 0 to 4 and, where m is an integer from 2 to 4, each R.sup.6 may be the same or different; and
n represents an integer from 0 to 4 and, where n is an integer from 2 to 4, each R.sup.3 may be the same or different;

55. A herbicidal composition comprising an effective amount of a herbicidal agent in admixture with an agriculturally or horticulturally acceptable carrier or diluent, wherein the herbicidal agent is a compound of formula (I): ##STR19## wherein: R.sup.1 represents:

an alkyl group having from 1 to 6 carbon atoms, said alkyl group being up substituted or being substituted by an alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
a cycloalkyl group having from 3 to 6 carbon atoms;
an alkoxy group having from 1 to 6 carbon atoms, said alkoxy group being unsubstituted or being substituted by from 1 to 4 halogen atoms; or
an alkylthio group having from 1 to 6 carbon atoms, said alkylthio group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
R.sup.2 represents:
a hydrogen atom;
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by a hydroxy group or by from 1 to 4 halogen atoms;
a cycloalkyl group having from 3 to 6 carbon atoms;
an alkenyl group having from 2 to 6 carbon atoms, said alkenyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
an alkynyl group having from 2 to 6 carbon atoms, said alkynyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms; or
a group represented by the formula --YR.sup.7;
R.sup.3 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
a cycloalkyl group having from 3 to 6 carbon atoms;
an alkoxy group having from 1 to 6 carbon atoms, said alkoxy group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
an alkenyl group having from 2 to 6 carbon atoms, said alkenyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
an alkynyl group having from 2 to 6 carbon atoms, said alkynyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
a halogen atom;
a nitro group; or
a group of formula --COR.sup.8, wherein R.sup.8 represents a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms, a cycloalkyl group having from 3 to 6 carbon atoms or an alkoxy group having from 1 to 6 carbon atoms;
R.sup.4 and R.sup.5 are the same or different and each represents a hydrogen atom or an alkyl group having from 1 to 6 carbon atoms;
R.sup.6 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
a cycloalkyl group having from 3 to 6 carbon atoms;
an alkoxy group having from 1 to 6 carbon atoms, said alkoxy group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
an alkenyl group having from 2 to 6 carbon atoms, said alkenyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
an alkynyl group having from 2 to 6 carbon atoms, said alkynyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
a halogen atom;
a nitro group; or
a group of formula --COR.sup.8, wherein R.sup.8 represents a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms, a cycloalkyl group having from 3 to 6 carbon atoms or an alkoxy group having from 1 to 6 carbon atoms;
A represents an oxygen atom or a sulfur atom;
X represents an oxygen atom or a sulfur atom;
Y represents a group selected from the group consisting of the groups of formulae --CO--, --COO--, --CH.sub.2 O--, --CH.sub.2 S--, --CH.sub.2 CH.sub.2 O--, --CH.sub.2 CH.sub.2 S--, --CH.sub.2 CO--, --CH.sub.2 COO--, --CH(Me)COO--, --CH.sub.2 CH.sub.2 CO--, --CH.sub.2 OCO--, CH.sub.2 OCOO-- and --CH.sub.2 CH.sub.2 OCO--;
R.sup.7 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 6 carbon atoms, an alkylthio group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
a cycloalkyl group having from 3 to 6 carbon atoms;
an alkenyl group having from 2 to 6 carbon atoms, said alkenyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
an alkynyl group having from 2 to 6 carbon atoms, said alkynyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
a carbocyclic aryl group having from 6 to 14 ring carbon atoms, said aryl group being unsubstituted or being substituted by at least one substituent selected from the group consisting of alkyl groups having from 1 to 6 carbon atoms, alkoxy groups having from 1 to 6 carbon atoms and halogen atoms;
an aralkyl group wherein the aryl moiety is a carbocyclic aryl group having from 6 to 10 ring carbon atoms which is unsubstituted or is substituted by from 1 to 4 halogen atoms, and the alkyl moiety has from 1 to 6 carbon atoms; or
a heterocyclic group having from 4 to 10 ring atoms including at least one ring heteroatom selected from the group consisting of oxygen atoms, sulfur atoms and nitrogen atoms, said heterocyclic group being fully unsaturated, partly unsaturated or saturated and being either unsubstituted, substituted by at least one substituent selected from alkyl groups having from 1 to 6 carbon atoms, alkoxy groups having from 1 to 6 carbon atoms and halogen atoms, or fused with a carbocyclic aryl group having from 6 to 10 ring carbon atoms;
Q represents an oxygen atom or a sulfur atom;
m represents an integer from 0 to 4 and, where m is an integer from 2 to 4, each R.sup.6 may be the same or different; and
n represents an integer from 0 to 4 and, where n is an integer from 2 to 4, each R.sup.3 may be the same or different;
or a herbicidally acceptable addition salt thereof.

56. The composition according to claim 55, wherein:

R.sup.1 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
a cycloalkyl group having from 3 to 6 carbon atoms; or
an alkoxy group having from 1 to 6 carbon atoms, said alkoxy group being unsubstituted or being substituted by from 1 to 4 halogen atoms.

57. The composition according to claim 55, wherein:

R.sup.1 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms; or
an unsubstituted alkoxy group having from 1 to 6 carbon atoms.

58. The composition according to claim 55, wherein:

R.sup.1 represents:
an alkyl group having from 1 to 3 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 3 carbon atoms; or
an unsubstituted alkoxy group having from 1 to 3 carbon atoms.

59. The composition according to claim 55, wherein R.sup.1 represents a methyl group or a methoxy group.

60. The composition according to claim 55, wherein R.sup.1 represents a methoxy group.

61. The composition according to claim 55, wherein:

R.sup.2 represents:
a hydrogen atom;
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by a hydroxy group or by from 1 to 4 halogen atoms;
a cycloalkyl group having from 3 to 6 carbon atoms; or
a group represented by the formula --YR.sup.7, as defined in claim 55.

62. The composition according to claim 55, wherein:

R.sup.2 represents:
a hydrogen atom;
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by a hydroxy group; or
a group represented by the formula --YR.sup.7, as defined in claim 55.

63. The composition according to claim 55, wherein:

R.sup.2 represents:
a hydrogen atom;
an alkyl group having from 1 to 3 carbon atoms which is substituted by a hydroxy group; or
a group represented by the formula --YR.sup.7, as defined in claim 55.

64. The composition according to claim 55, wherein R.sup.2 represents a hydrogen atom, a hydroxymethyl group or a group represented by the formula --YR.sup.7, as defined in claim 55.

65. The composition according to claim 55, wherein R.sup.2 represents a hydrogen atom.

66. The composition according to claim 55, wherein Y represents a group selected from the group consisting of the groups of formulae --CO--, --COO--, --CH.sub.2 O--, --CH.sub.2 CH.sub.2 O--, --CH.sub.2 CO--, --CH.sub.2 COO--, --CH.sub.2 CH.sub.2 CO--, --CH.sub.2 OCO--, --CH.sub.2 OCOO-- and --CH.sub.2 CH.sub.2 OCO--.

67. The composition according to claim 55, wherein Y represents a group selected from the group consisting of the groups of formulae --CO--, --COO--, --CH.sub.2 O--, --CH.sub.2 CH.sub.2 O--, --CH.sub.2 OCO-- and --CH.sub.2 OCOO--.

68. The composition according to claim 55, wherein Y represents a group selected from the group consisting of the groups of formulae --CO--, --COO--, --CH.sub.2 O--, --CH.sub.2 OCO--, and --CH.sub.2 OCOO--.

69. The composition according to claim 55, wherein Y represents a group selected from the group consisting of the groups of formulae --CO--, --COO-- and --CH.sub.2 OCO--.

70. The composition according to claim 55, wherein:

R.sup.7 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
a cycloalkyl group having from 3 to 6 carbon atoms;
an alkenyl group having from 2 to 6 carbon atoms, said alkenyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
an alkynyl group having from 2 to 6 carbon atoms, said alkynyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
a carbocyclic aryl group having from 6 to 14 ring carbon atoms, said aryl group being unsubstituted or being substituted by from 1 to 3 alkyl groups having from 1 to 6 carbon atoms, 1 to 3 alkoxy groups having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
an aralkyl group wherein the aryl moiety is a carbocyclic aryl group having from 6 to 14 ring carbon atoms, said aryl group being unsubstituted or being substituted by from 1 to 4 halogen atoms, and the alkyl moiety has from 1 to 6 carbon atoms; or
a heterocyclic group having from 4 to 10 ring atoms including at least one ring heteroatom selected from the group consisting of oxygen atoms, sulfur atoms and nitrogen atoms, said heterocyclic group being fully unsaturated, partly unsaturated or saturated and being either unsubstituted, substituted by at least one substituent selected from alkyl groups having from 1 to 6 carbon atoms, alkoxy groups having from 1 to 6 carbon atoms and halogen atoms, or fused with a carbocyclic aryl group having from 6 to 10 ring carbon atoms.

71. The composition according to claim 55, wherein R.sup.7 represents an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms.

72. The composition according to claim 55, wherein R.sup.7 represents an alkyl group having from 1 to 3 carbon atoms, said alkyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms.

73. The composition according to claim 55, wherein R.sup.7 represents an ethyl group or a 2,2,2-trichloroethyl group.

74. The composition according to claim 55, wherein:

R.sup.3 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by a alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
a cycloalkyl group having from 3 to 6 carbon atoms;
an alkoxy group having from 1 to 6 carbon atoms, said alkoxy group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
a halogen atom;
a nitro group; or
a group represented by the formula --COR.sup.8, as defined in claim 55.

75. The composition according to claim 55, wherein:

R.sup.3 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
an alkoxy group having from 1 to 6 carbon atoms, said alkoxy group being;
unsubstituted or being substituted by from 1 to 4 halogen atoms; or
a halogen atom.

76. The composition according to claim 55, wherein:

R.sup.3 represents:
an unsubstituted alkyl group having from 1 to 3 carbon atoms;
an alkoxy group having from 1 to 3 carbon atoms; or
a halogen atom.

77. The composition according to claim 55, wherein R.sup.3 represents a methyl group, an ethyl group, a methoxy group, an ethoxy group, a fluorine atom or a chlorine atom.

78. The composition according to claim 55, wherein R.sup.3 represents a methyl group.

79. The composition according to claim 55, wherein R.sup.4 and R.sup.5 are the same or different and each represents a hydrogen atom or a methyl group.

80. The composition according to claim 55, wherein R.sup.4 represents a hydrogen atom or a methyl group and R.sup.5 represents a hydrogen atom.

81. The composition according to claim 55, wherein R.sup.4 and R.sup.5 each represent a hydrogen atom.

82. The composition according to claim 55, wherein:

R.sup.6 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by a alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
a cycloalkyl group having from 3 to 6 carbon atoms;
an alkoxy group having from 1 to 6 carbon atoms, said alkoxy group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
a halogen atom; or
a group represented by the formula --COR.sup.8, as defined in claim 55.

83. The composition according to claim 55, wherein:

R.sup.6 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
an alkoxy group having from 1 to 6 carbon atoms, said alkoxy group being unsubstituted or being substituted by from 1 to 4 halogen atoms; or
a halogen atom.

84. The composition according to claim 55, wherein:

R.sup.6 represents:
an unsubstituted alkyl group having from 1 to 3 carbon atoms;
an unsubstituted alkoxy group having from 1 to 3 carbon atoms; or
a halogen atom.

85. The composition according to claim 55, wherein R.sup.6 represents a methoxy group, a fluorine atom or a chlorine atom.

86. The composition according to claim 55, wherein R.sup.6 represents a fluorine atom or a chlorine atom.

87. The composition according to claim 55, wherein R.sup.8 represents an alkyl group having from 1 to 3 carbon atoms or an alkoxy group having from 1 to 3 carbon atoms.

88. The composition according to claim 55, wherein R.sup.8 represents an alkoxy group having from 1 to 3 carbon atoms.

89. The composition according to claim 55, wherein R.sup.8 represents a methoxy group.

90. The composition according to claim 55, wherein A represents an oxygen atom.

91. The composition according to claim 55, wherein X represents an oxygen atom.

92. The composition according to claim 55, wherein Q represents a sulfur atom.

93. The composition according to claim 55, wherein m represents an integer from 0 to 3.

94. The composition according to claim 55, wherein m represents an integer of 0 or 1.

95. The composition according to claim 55, wherein m represents an integer of 0.

96. The composition according to claim 55, wherein n represents an integer from 0 to 3.

97. The composition according to claim 55, wherein n represents an integer from 0 to 2.

98. The composition according to claim 55, wherein n represents an integer of 0 or 1.

99. The composition according to claim 55, wherein n represents an integer of 1.

100. The composition according to claim 55 wherein:

R.sup.1 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
a cycloalkyl group having from 3 to 6 carbon atoms; or
an alkoxy group having from 1 to 6 carbon atoms, said alkoxy group being; unsubstituted or being substituted by from 1 to 4 halogen atoms;
R.sup.2 represents:
a hydrogen atom;
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being
unsubstituted or being substituted by a hydroxy group or by from 1 to 4 halogen atoms;
a cycloalkyl group having from 3 to 6 carbon atoms; or
a group represented by the formula --YR.sup.7, wherein:
Y represents a group selected from the group consisting of the the groups of formulae --CO--, --COO--, --CH.sub.2 O--, --CH.sub.2 CH.sub.2 O--, --CH.sub.2 CO--, --CH.sub.2 COO--, --CH.sub.2 CH.sub.2 CO--, --CH.sub.2 OCO--, --CH.sub.2 OCOO-- and --CH.sub.2 CH.sub.2 OCO--, and
R.sup.7 represents an.alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms,
a cycloalkyl group having from 3 to 6 carbon atoms,
an alkenyl group having from 2 to 6 carbon atoms, said alkenyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms,
an alkynyl group having from 2 to 6 carbon atoms, said alkynyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms,
a carbocyclic aryl group having from 6 to 14 ring carbon atoms, said aryl group being unsubstituted or being substituted by from 1 to 3 alkyl groups having from 1 to 6 carbon atoms, 1 to 3 alkoxy groups having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms,
an aralkyl group wherein the aryl moiety is a carbocyclic aryl group having from 6 to 14 ring carbon atoms, said aryl group being unsubstituted or being substituted by from 1 to 4 halogen atoms, and the alkyl moiety has from 1 to 6 carbon atoms, or
a heterocyclic group having from 4 to 10 ring atoms including at least one ring heteroatom selected from the group consisting of oxygen atoms, sulfur atoms and nitrogen atoms, said heterocyclic group being fully unsaturated, partly unsaturated or saturated and being either unsubstituted, substituted by at least one substituent selected from alkyl groups having from 1 to 6 carbon atoms,
alkoxy groups having from 1 to 6 carbon atoms and halogen atoms, or fused with a carbocyclic aryl group having from 6 to 10 ring carbon atoms;
R.sup.3 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by a alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
a cycloalkyl group having from 3 to 6 carbon atoms;
an alkoxy group having from 1 to 6 carbon atoms, said alkoxy group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
a halogen atom;
a nitro group; or
a group represented by the formula --COR.sup.8, wherein R.sup.8 represents an alkyl group having from 1 to 3 carbon atoms or an alkoxy group having from 1 to 3 carbon atoms;
R.sup.4 and R.sup.5 are the same or different and each represents a hydrogen atom or a methyl group;
R.sup.6 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by a alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
a cycloalkyl group having from 3 to 6 carbon atoms;
an alkoxy group having from 1 to 6 carbon atoms, said alkoxy group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
a halogen atom; or
a group represented by the formula --COR.sup.8, wherein R.sup.8 represents an alkyl group having from 1 to 3 carbon atoms or an alkoxy group having from 1 to 3 carbon atoms; and
m and n are the same or different and each represents an integer from 0 to 3.

101. The composition according to claim 55 wherein:

R.sup.1 represents:
an alkyl group having from 1 to 6 carbon atoms; said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms; or
an unsubstituted alkoxy group having from 1 to 6 carbon atoms;
R.sup.2 represents:
a hydrogen atom;
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by a hydroxy group; or
a group represented by the formula --YR.sup.7, wherein Y represents a group selected from the group consisting of the groups of formulae --CO--, --COO--, --CH.sub.2 O--, --CH.sub.2 CH.sub.2 O--, --CH.sub.2 OCO-- and --CH.sub.2 OCOO-- and R.sup.7 represents an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
R.sup.3 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
an alkoxy group having from 1 to 6 carbon atoms, said alkoxy group being unsubstituted or being substituted by from 1 to 4 halogen atoms; or
a halogen atom;
R.sup.4 and R.sup.5 are the same or different and each represents a hydrogen atom or a methyl group;
R.sup.6 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
an alkoxy group having from 1 to 6 carbon atoms, said alkoxy group being unsubstituted or being substituted by from 1 to 4 halogen atoms; or
a halogen atom; and
m represents an integer from 0 to 3 and n represents an integer from 0 to 2.

102. The composition according to claim 55 wherein:

R.sup.1 represents:
an alkyl group having from 1 to 3 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 3 carbon atoms; or
an unsubstituted alkoxy group having from 1 to 3 carbon atoms;
R.sup.2 represents:
a hydrogen atom;
an alkyl group having from 1 to 3 carbon atoms which is substituted by a hydroxy group; or
a group represented by the formula --YR.sup.7, wherein Y represents a group selected from the group consisting of the groups of formulae --CO--, --COO--, --CH.sub.2 O--, --CH.sub.2 OCO-- and --CH.sub.2 OCOO-- and R.sup.7 represents an alkyl group having from 1 to 3 carbon atoms, said alkyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
R.sup.3 represents:
an unsubstituted alkyl group having from 1 to 3 carbon atoms;
an alkoxy group having from 1 to 3 carbon atoms; or
a halogen atom;
R.sup.4 represents a hydrogen atom or a methyl group and R.sup.5 represents a hydrogen atom;
R.sup.6 represents:
an unsubstituted alkyl group having from 1 to 3 carbon atoms;
an unsubstituted alkoxy group having from 1 to 3 carbon atoms; or
a halogen atom; and
m and n are the same or different and each represents an integer of 0 or 1.

103. The composition according to claim 55 wherein:

R.sup.1 represents a methyl group or a methoxy group;
R.sup.2 represents a hydrogen atom, a hydroxymethyl group or a group represented by the formula --YR.sup.7, wherein Y represents a group selected from the group consisting of the groups of formulae --CO--, --COO-- or --CH.sub.2 OCO-- and R.sup.7 represents an ethyl group or a 2,2,2-trichloroethyl group;
R.sup.3 represents a methyl group, an ethyl group, a methoxy group, an ethoxy group, a fluorine atom or a chlorine atom;
R.sup.4 represents a hydrogen atom or a methyl group and R.sup.5 represents a hydrogen atom;
R.sup.6 represents a methoxy group, a fluorine atom or a chlorine atom;
m and n are the same or different and each represents an integer of 0 or 1;
A represents an oxygen atom;
X represents an oxygen atom; and
Q represents a sulfur atom.

104. The composition according to claim 55 wherein:

R.sup.1 represents a methoxy group;
R.sup.2 represents a hydrogen atom;
R.sup.3 represents a methyl group;
R.sup.4 and R.sup.5 each represent a hydrogen atom;
m represents an integer of 0;
n represents an integer of 1;
A represents an oxygen atom;
X represents an oxygen atom; and
Q represents a sulfur atom.

105. The composition according to claim 55 wherein m represents an integer of 1 and R.sup.3 is at the 2-position of the phenyl ring.

106. The composition according to claim 55, wherein:

R.sup.1 represents an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
R.sup.2 represents:
a hydrogen atom;
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
an alkenyl group having from 3 to 6 carbon atoms, said alkenyl group being unsubstituted;
an alkynyl group having from 3 to 6 carbon atoms, said alkynyl group being unsubstituted; or
an alkoxycarbonyl group wherein the alkoxy moiety has from 1 to 6 carbon atoms;
R.sup.3 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
an alkoxy group having from 1 to 6 carbon atoms, said alkoxy group being unsubstituted;
an alkenyl group having from 3 to 6 carbon atoms, said alkenyl group being unsubstituted;
an alkynyl group having from 3 to 6 carbon atoms, said alkynyl group being unsubstituted;
a halogen atom;
a nitro group; or
a formyl group;
R.sup.4 and R.sup.5 are the same or different and each represents a hydrogen atom or an alkyl group having from 1 to 6 carbon atoms;
R.sup.6 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
an alkoxy group having from 1 to 6 carbon atoms, said alkoxy group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
an alkenyl group having from 3 to 6 carbon atoms, said alkenyl group being unsubstituted;
an alkynyl group having from 3 to 6 carbon atoms, said alkynyl group being unsubstituted; or
a halogen atom;
A represents an oxygen atom or a sulfur atom;
X represents an oxygen atom;
Q represents a sulfur atom;
m represents an integer from 0 to 4 and, where m is an integer from 2 to 4, each R.sup.6 may be the same or different; and
n represents an integer from 0 to 4 and, where n is an integer from 2 to 4, each R.sup.3 may be the same or different;

107. The composition according to claim 55, wherein:

R.sup.1 represents:
an alkoxy group having from 1 to 6 carbon atoms, said alkoxy group being unsubstituted or being substituted by from 1 to 4 halogen atoms; or
an alkylthio group having from 1 to 6 carbon atoms, said alkylthio group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
R.sup.2 represents:
a hydrogen atom; or
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
R.sup.3 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
an alkoxy group having from 1 to 6 carbon atoms, said alkoxy group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
a halogen atom;
a nitro group; or
a formyl group;
R.sup.4 and R.sup.5 are the same or different and each represents a hydrogen atom or an alkyl group having from 1 to 6 carbon atoms;
R.sup.6 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
an alkoxy group having from 1 to 6 carbon atoms, said alkoxy group being unsubstituted or being substituted by from 1 to 4 halogen atoms; or
a halogen atom;
A represents an oxygen atom or a sulfur atom;
X represents an oxygen atom or a sulfur atom;
Q represents an oxygen atom or a sulfur atom;
m represents an integer from 0 to 4 and, where m is an integer from 2 to 4, each R.sup.6 may be the same or different; and
n represents an integer from 0 to 4 and, where n is an integer from 2 to 4, each R.sup.3 may be the same or different;

109. A method of destroying weeds, either before or after germination of said weeds, by administering a herbicidal agent to a locus including said germinated or ungerminated weeds, wherein the herbicidal agent is a compound of formula (I): ##STR20## wherein: R.sup.1 represents:

an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
a cycloalkyl group having from 3 to 6 carbon atoms;
an alkoxy group having from 1 to 6 carbon atoms, said alkoxy group being unsubstituted or being substituted by from 1 to 4 halogen atoms; or
an alkylthio group having from 1 to 6 carbon atoms, said alkylthio group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
R.sup.2 represents:
a hydrogen atom;
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by a hydroxy group or by from 1 to 4 halogen atoms;
a cycloalkyl group having from 3 to 6 carbon atoms;
an alkenyl group having from 2 to 6 carbon atoms, said alkenyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
an alkynyl group having from 2 to 6 carbon atoms, said alkynyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms; or
a group represented by the formula --YR.sup.7;
R.sup.3 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
a cycloalkyl group having from 3 to 6 carbon atoms;
an alkoxy group having from 1 to 6 carbon atoms, said alkoxy group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
an alkenyl group having from 2 to 6 carbon atoms, said alkenyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
an alkynyl group having from 2 to 6 carbon atoms, said alkynyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
a halogen atom;
a nitro group; or
a group of formula --COR.sup.8, wherein R.sup.8 represents a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms, a cycloalkyl group having from 3 to 6 carbon atoms or an alkoxy group having from 1 to 6 carbon atoms;
R.sup.4 and R.sup.5 are the same or different and each represents a hydrogen atom or an alkyl group having from 1 to 6 carbon atoms;
R.sup.6 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
a cycloalkyl group having from 3 to 6 carbon atoms;
an alkoxy group having from 1 to 6 carbon atoms, said alkoxy group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
an alkenyl group having from 2 to 6 carbon atoms, said alkenyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
an alkynyl group having from 2 to 6 carbon atoms, said alkynyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
a halogen atom;
a nitro group; or
a group of formula --COR.sup.8, wherein R.sup.8 represents a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms, a cycloalkyl group having from 3 to 6 carbon atoms or an alkoxy group having from 1 to 6 carbon atoms;
A represents an oxygen atom or a sulfur atom;
X represents an oxygen atom or a sulfur atom;
Y represents a group selected from the group consisting of the groups of formulae --CO--, --COO--, --CH.sub.2 O--, --CH.sub.2 S--, --CH.sub.2 CH.sub.2 O--, --CH.sub.2 CH.sub.2 S--, --CH.sub.2 CO--, --CH.sub.2 COO--, --CH(Me)COO--, --CH.sub.2 CH.sub.2 CO--, --CH.sub.2 OCO--, CH.sub.2 OCOO-- and --CH.sub.2 CH.sub.2 OCO--;
R.sup.7 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 6 carbon atoms, an alkylthio group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
a cycloalkyl group having from 3 to 6 carbon atoms;
an alkenyl group having from 2 to 6 carbon atoms, said alkenyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
an alkynyl group having from 2 to 6 carbon atoms, said alkynyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
a carbocyclic aryl group having from 6 to 14 ring carbon atoms, said aryl group being unsubstituted or being substituted by at least one substituent selected from the group consisting of alkyl groups having from 1 to 6 carbon atoms, alkoxy groups having from 1 to 6 carbon atoms and halogen atoms;
an aralkyl group wherein the aryl moiety is a carbocyclic aryl group having from 6 to 10 ring carbon atoms which is unsubstituted or is substituted by from 1 to 4 halogen atoms, and the alkyl moiety has from 1 to 6 carbon atoms; or
a heterocyclic group having from 4 to 10 ring atoms including at least one ring heteroatom selected from the group consisting of oxygen atoms, sulfur atoms and nitrogen atoms, said heterocyclic group being fully unsaturated, partly unsaturated or saturated and being either unsubstituted, substituted by at least one substituent selected from alkyl groups having from 1 to 6 carbon atoms, alkoxy groups having from 1 to 6 carbon atoms and halogen atoms, or fused with a carbocyclic aryl group having from 6 to 10 ring carbon atoms;
Q represents an oxygen atom or a sulfur atom;
m represents an integer from 0 to 4 and, where m is an integer from 2 to 4, each R.sup.6 may be the same or different; and
n represents an integer from 0 to 4 and, where n is an integer from 2 to 4, each R.sup.3 may be the same or different;
or a herbicidally acceptable addition salt thereof.

110. The method according to claim 109, wherein:

R.sup.1 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
a cycloalkyl group having from 3 to 6 carbon atoms; or
an alkoxy group having from 1 to 6 carbon atoms, said alkoxy group being unsubstituted or being substituted by from 1 to 4 halogen atoms.

111. The method according to claim 109, wherein:

R.sup.1 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms; or
an unsubstituted alkoxy group having from 1 to 6 carbon atoms.

112. The method according to claim 109, wherein:

R.sup.1 represents:
an alkyl group having from 1 to 3 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 3 carbon atoms; or
an unsubstituted alkoxy group having from 1 to 3 carbon atoms.

113. The method according to claim 109, wherein R.sup.1 represents a methyl group or a methoxy group.

114. The method according to claim 109, wherein R.sup.1 represents a methoxy group.

115. The method according to claim 109, wherein:

R.sup.2 represents:
a hydrogen atom;
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by a hydroxy group or by from 1 to 4 halogen atoms;
a cycloalkyl group having from 3 to 6 carbon atoms; or
a group represented by the formula --YR.sup.7, as defined in claim 109.

116. The method according to claim 109, wherein:

R.sup.2 represents:
a hydrogen atom;
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by a hydroxy group; or
a group represented by the formula --YR.sup.7, as defined in claim 109.

117. The method according to claim 109, wherein:

R.sup.2 represents:
a hydrogen atom;
an alkyl group having from 1 to 3 carbon atoms which is substituted by a hydroxy group; or
a group represented by the formula --YR.sup.7, as defined in claim 109.

118. The method according to claim 109, wherein R.sup.2 represents a hydrogen atom, a hydroxymethyl group or a group represented by the formula --YR.sup.7, as defined in claim 109.

119. The method according to claim 109, wherein R.sup.2 represents a hydrogen atom.

120. The method according to claim 109, wherein Y represents a group selected from the group consisting of the groups of formulae --CO--, --COO--, --CH.sub.2 O--, --CH.sub.2 CH.sub.2 O, --CH.sub.2 CO--, --CH.sub.2 COO--, --CH.sub.2 CH.sub.2 CO--, --CH.sub.2 OCO--, --CH.sub.2 OCOO-- and --CH.sub.2 CH.sub.2 OCO--.

121. The method according to claim 109, wherein Y represents a group selected from the group consisting of the groups of formulae --CO--, --COO--, --CH.sub.2 O--, --CH.sub.2 CH.sub.2 O--, --CH.sub.2 OCO-- and --CH.sub.2 OCOO--.

122. The method according to claim 109, wherein Y represents a group selected from the group consisting of the groups of formulae --CO--, --COO--, --CH.sub.2 O--, --CH.sub.2 OCO-- and --CH.sub.2 OCOO--.

123. The method according to claim 109, wherein Y represents a group selected from the group consisting of the groups of formulae --CO--, --COO-- and --CH.sub.2 OCO--.

124. The method according to claim 109, wherein:

R.sup.7 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
a cycloalkyl group having from 3 to 6 carbon atoms;
an alkenyl group having from 2 to 6 carbon atoms, said alkenyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
an alkynyl group having from 2 to 6 carbon atoms, said alkynyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
a carbocyclic aryl group having from 6 to 14 ring carbon atoms, said aryl group being unsubstituted or being substituted by from 1 to 3 alkyl groups having from 1 to 6 carbon atoms, 1 to 3 alkoxy groups having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
an aralkyl group wherein the aryl moiety is a carbocyclic aryl group having from 6 to 14 ring carbon atoms, said aryl group being unsubstituted or being substituted by from 1 to 4 halogen atoms, and the alkyl moiety has from 1 to 6 carbon atoms; or
a heterocyclic group having from 4 to 10 ring atoms including at least one ring heteroatom selected from the group consisting of oxygen atoms, sulfur atoms and nitrogen atoms, said heterocyclic group being fully unsaturated, partly unsaturated or saturated and being either unsubstituted, substituted by at least one substituent selected from alkyl groups having from 1 to 6 carbon atoms, alkoxy groups having from 1 to 6 carbon atoms and halogen atoms, or fused with a carbocyclic aryl group having from 6 to 10 ring carbon atoms.

125. The method according to claim 109, wherein R.sup.7 represents an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms.

126. The method according to claim 109, wherein R.sup.7 represents an alkyl group having from 1 to 3 carbon atoms, said alkyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms.

127. The method according to claim 109, wherein R.sup.7 represents an ethyl group or a 2,2,2-trichloroethyl group.

128. The method according to claim 109, wherein:

R.sup.3 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by a alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
a cycloalkyl group having from 3 to 6 carbon atoms;
an alkoxy group having from 1 to 6 carbon atoms, said alkoxy group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
a halogen atom;
a nitro group; or
a group represented by the formula --COR.sup.8, as defined in claim 109.

129. The method according to claim 109, wherein:

R.sup.3 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
an alkoxy group having from 1 to 6 carbon atoms, said alkoxy group being unsubstituted or being substituted by from 1 to 4 halogen atoms; or
a halogen atom.

130. The method according to claim 109, wherein:

R.sup.3 represents:
an unsubstituted alkyl group having from 1 to 3 carbon atoms;
an alkoxy group having from 1 to 3 carbon atoms; or
a halogen atom.

131. The method according to claim 109, wherein R.sup.3 represents a methyl group, an ethyl group, a methoxy group, an ethoxy group, a fluorine atom or a chlorine atom.

132. The method according to claim 109, wherein R.sup.3 represents a methyl group.

133. The method according to claim 109, wherein R.sup.4 and R.sup.5 are the same or different and each represents a hydrogen atom or a methyl group.

134. The method according to claim 109, wherein R.sup.4 represents a hydrogen atom or a methyl group and R.sup.5 represents a hydrogen atom.

135. The method according to claim 109, wherein R.sup.4 and R.sup.5 each represent a hydrogen atom.

136. The method according to claim 109, wherein:

R.sup.6 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by a alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
a cycloalkyl group having from 3 to 6 carbon atoms;
an alkoxy group having from 1 to 6 carbon atoms, said alkoxy group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
a halogen atom; or
a group represented by the formula --COR.sup.8, as defined in claim 109.

137. The method according to claim 109, wherein:

R.sup.6 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
an alkoxy group having from 1 to 6 carbon atoms, said alkoxy group being unsubstituted or being substituted by from 1 to 4 halogen atoms; or
a halogen atom.

138. The method according to claim 109, wherein:

R.sup.6 represents:
an unsubstituted alkyl group having from 1 to 3 carbon atoms;
an unsubstituted alkoxy group having from 1 to 3 carbon atoms; or
a halogen atom.

139. The method according to claim 109, wherein R.sup.6 represents a methoxy group, a fluorine atom or a chlorine atom.

140. The method according to claim 109, wherein R.sup.6 represents a fluorine atom or a chlorine atom.

141. The method according to claim 109, wherein R.sup.8 represents an alkyl group having from 1 to 3 carbon atoms or an alkoxy group having from 1 to 3 carbon atoms.

142. The method according to claim 109, wherein R.sup.8 represents an alkoxy group having from 1 to 3 carbon atoms.

143. The method according to claim 109, wherein R.sup.8 represents a methoxy group.

144. The method according to claim 109, wherein A represents an oxygen atom.

145. The method according to claim 109, wherein X represents an oxygen atom.

146. The method according to claim 109, wherein Q represents a sulfur atom.

147. The method according to claim 109, wherein m represents an integer from 0 to 3.

148. The method according to claim 109, wherein m represents an integer of 0 or 1.

149. The method according to claim 109, wherein m represents an integer of 0.

150. The method according to claim 109, wherein n represents an integer from 0 to 3.

151. The method according to claim 109, wherein n represents an integer from. 0 to 2.

152. The method according to claim 109, wherein n represents an integer of 0 or 1.

153. The method according to claim 109, wherein n represents an integer of 1.

154. The method according to claim 109 wherein:

R.sup.1 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
a cycloalkyl group having from 3 to 6 carbon atoms; or
an alkoxy group having from 1 to 6 carbon atoms, said alkoxy group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
R.sup.2 represents:
a hydrogen atom;
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by a hydroxy group or by from 1 to 4 halogen atoms;
a cycloalkyl group having from 3 to 6 carbon atoms; or
a group represented by the formula --YR.sup.7, wherein:
Y represents a group selected from the group consisting of the the groups of formulae --CO--, --COO--, --CH.sub.2 --, --CH.sub.2 CH.sub.2 O--, --CH.sub.2 CO--, --CH.sub.2 COO--, --CH.sub.2 CH.sub.2 CO--, --CH.sub.2 OCO--, --CH.sub.2 OCOO-- and --CH.sub.2 CH.sub.2 OCO--, and
R.sup.7 represents an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms,
a cycloalkyl group having from 3 to 6 carbon atoms,
an alkenyl group having from 2 to 6 carbon atoms, said alkenyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms,
an alkynyl group having from 2 to 6 carbon atoms, said alkynyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms,
a carbocyclic aryl group having from 6 to 14 ring carbon atoms, said aryl group being unsubstituted or being substituted by from 1 to 3 alkyl groups having from 1 to 6 carbon atoms, 1 to 3 alkoxy groups having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms,
an aralkyl group wherein the aryl moiety is a carbocyclic aryl group having from 6 to 14 ring carbon atoms, said aryl group being unsubstituted or being substituted by from 1 to 4 halogen atoms, and the alkyl moiety has from 1 to 6 carbon atoms, or
a heterocyclic group having from 4 to 10 ring atoms including at least one ring heteroatom selected from the group consisting of oxygen atoms, sulfur atoms and nitrogen atoms, said heterocyclic group being fully unsaturated, partly unsaturated or saturated and being either unsubstituted, substituted by at least one substituent selected from alkyl groups having from 1 to 6 carbon atoms,
alkoxy groups having from 1 to 6 carbon atoms and halogen atoms, or fused with a carbocyclic aryl group having from 6 to 10 ring carbon atoms;
R.sup.3 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by a alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
a cycloalkyl group having from 3 to 6 carbon atoms;
an alkoxy group having from 1 to 6 carbon atoms, said alkoxy group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
a halogen atom;
a nitro group; or
a group represented by the formula --COR.sup.8, wherein R.sup.8 represents an alkyl group having from 1 to 3 carbon atoms or an alkoxy group having from 1 to 3 carbon atoms;
R.sup.4 and R.sup.5 are the same or different and each represents a hydrogen atom or a methyl group;
R.sup.6 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by a alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
a cycloalkyl group having from 3 to 6 carbon atoms;
an alkoxy group having from 1 to 6 carbon atoms, said alkoxy group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
a halogen atom; or
a group represented by the formula --COR.sup.8, wherein R.sup.8 represents an alkyl group having from 1 to 3 carbon atoms or an alkoxy group having from 1 to 3 carbon atoms; and
m and n are the same or different and each represents an integer from 0 to 3.

155. The method according to claim 109 wherein:

R.sup.1 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms; or
an unsubstituted alkoxy group having from 1 to 6 carbon atoms;
R.sup.2 represents:
a hydrogen atom;
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by a hydroxy group; or
a group represented by the formula --YR.sup.7, wherein Y represents a group selected from the group consisting of the groups of formulae --CO--, --COO--, --CH.sub.2 O--, --CH.sub.2 CH.sub.2 O--, --CH.sub.2 OCO-- and --CH.sub.2 OCOO-- and R.sup.7 represents an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
R.sup.3 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
an alkoxy group having from 1 to 6 carbon atoms, said alkoxy group being unsubstituted or being substituted by from 1 to 4 halogen atoms; or
a halogen atom;
R.sup.4 and R.sup.5 are the same or different and each represents a hydrogen atom or a methyl group;
R.sup.6 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
an alkoxy group having from 1 to 6 carbon atoms, said alkoxy group being unsubstituted or being substituted by from 1 to 4 halogen atoms; or
a halogen atom; and
m represents an integer from 0 to 3 and n represents an integer from 0 to 2.

156. The method according to claim 109 wherein:

R.sup.1 represents:
an alkyl group having from 1 to 3 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 3 carbon atoms; or
an unsubstituted alkoxy group having from 1 to 3 carbon atoms;
R.sup.2 represents:
a hydrogen atom;
an alkyl group having from 1 to 3 carbon atoms which is substituted by a hydroxy group; or
a group represented by the formula --YR.sup.7, wherein Y represents a group selected from the group consisting of the groups of formulae --CO--, --COO--, --CH.sub.2 O--, --CH.sub.2 OCO-- and --CH.sub.2 OCOO-- and R.sup.7 represents an alkyl group having from 1 to 3 carbon atoms, said alkyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
R.sup.3 represents:
an unsubstituted alkyl group having from 1 to 3 carbon atoms;
an alkoxy group having from 1 to 3 carbon atoms; or
a halogen atom;
R.sup.4 represents a hydrogen atom or a methyl group and R.sup.5 represents a hydrogen atom;
R.sup.6 represents:
an unsubstituted alkyl group having from 1 to 3 carbon atoms;
an unsubstituted alkoxy group having from 1 to 3 carbon atoms; or
a halogen atom; and
m and n are the same or different and each represents an integer of 0 or 1.

157. The method according to claim 109 wherein:

R.sup.1 represents a methyl group or a methoxy group;
R.sup.2 represents a hydrogen atom, a hydroxymethyl group or a group represented by the formula --YR.sup.7, wherein Y represents a group selected from the group consisting of the groups of formulae --CO--, --COO-- or --CH.sub.2 OCO-- and R.sup.7 represents an ethyl group or a 2,2,2-trichloroethyl group;
R.sup.3 represents a methyl group, an ethyl group, a methoxy group, an ethoxy group, a fluorine atom or a chlorine atom;
R.sup.4 represents a hydrogen atom or a methyl group and R.sup.5 represents a hydrogen atom;
R.sup.6 represents a methoxy group, a fluorine atom or a chlorine atom;
m and n are the same or different and each represents an integer of 0 or 1;
A represents an oxygen atom;
X represents an oxygen atom; and
Q represents a sulfur atom.

158. The method according to claim 109 wherein:

R.sup.1 represents a methoxy group;
R.sup.2 represents a hydrogen atom;
R.sup.3 represents a methyl group;
R.sup.4 and R.sup.5 each represent a hydrogen atom;
m represents an integer of 0;
n represents an integer of 1;
A represents an oxygen atom;
X represents an oxygen atom; and
Q represents a sulfur atom.

159. The method according to claim 109 wherein m represents an integer of 1 and R.sup.3 is at the 2-position of the phenyl ring.

160. The method according to claim 109, wherein:

R.sup.1 represents an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
R.sup.2 represents:
a hydrogen atom;
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
an alkenyl group having from 3 to 6 carbon atoms, said alkenyl group being unsubstituted;
an alkynyl group having from 3 to 6 carbon atoms, said alkynyl group being unsubstituted; or
an alkoxycarbonyl group wherein the alkoxy moiety has from 1 to 6 carbon atoms;
R.sup.3 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
an alkoxy group having from 1 to 6 carbon atoms, said alkoxy group being unsubstituted;
an alkenyl group having from 3 to 6 carbon atoms, said alkenyl group being unsubstituted;
an alkynyl group having from 3 to 6 carbon atoms, said alkynyl group being unsubstituted;
a halogen atom;
a nitro group; or
a formyl group;
R.sup.4 and R.sup.5 are the same or different and each represents a hydrogen atom or an alkyl group having from 1 to 6 carbon atoms;
R.sup.6 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
an alkoxy group having from 1 to 6 carbon atoms, said alkoxy group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
an alkenyl group having from 3 to 6 carbon atoms, said alkenyl group being unsubstituted;
an alkynyl group having from 3 to 6 carbon atoms, said alkynyl group being unsubstituted; or
a halogen atom;
A represents an oxygen atom or a sulfur atom;
X represents an oxygen atom;
Q represents a sulfur atom;
m represents an integer from 0 to 4 and, where m is an integer from 2 to 4, each R.sup.6 may be the same or different; and
n represents an integer from 0 to 4 and, where n is an integer from 2 to 4, each R.sup.3 may be the same or different;

161. The method according to claim 109, wherein:

R.sup.1 represents:
an alkoxy group having from 1 to 6 carbon atoms, said alkoxy group being unsubstituted or being substituted by from 1 to 4 halogen atoms; or
an alkylthio group having from 1 to 6 carbon atoms, said alkylthio group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
R.sup.2 represents:
a hydrogen atom; or
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
R.sup.3 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
an alkoxy group having from 1 to 6 carbon atoms, said alkoxy group being unsubstituted or being substituted by from I to 4 halogen atoms;
a halogen atom;
a nitro group; or
a formyl group;
R.sup.4 and R.sup.5 are the same or different and each represents a hydrogen atom or an alkyl group having from 1 to 6 carbon atoms;
R.sup.6 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
an alkoxy group having from 1 to 6 carbon atoms, said alkoxy group being unsubstituted or being substituted by from 1 to 4 halogen atoms; or
a halogen atom;
A represents an oxygen atom or a sulfur atom;
X represents an oxygen atom or a sulfur atom;
Q represents an oxygen atom or a sulfur atom;
m represents an integer from 0 to 4 and, where m is an integer from 2 to 4, each R.sup.6 may be the same or different; and
n represents an integer from 0 to 4 and, where n is an integer from 2 to 4, each R.sup.3 may be the same or different;

163. A process for the preparation of a compound of formula (I): ##STR21## wherein: R.sup.1 represents:

an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
a cycloalkyl group having from 3 to 6 carbon atoms;
an alkoxy group having from 1 to 6 carbon atoms, said alkoxy group being unsubstituted or being substituted by from 1 to 4 halogen atoms; or
an alkylthio group having from 1 to 6 carbon atoms, said alkylthio group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
R.sup.2 represents:
a hydrogen atom;
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by a hydroxy group or by from 1 to 4 halogen atoms;
a cycloalkyl group having from 3 to 6 carbon atoms;
an alkenyl group having from 2 to 6 carbon atoms, said alkenyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
an alkynyl group having from 2 to 6 carbon atoms, said alkynyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms; or
a group represented by the formula --YR.sup.7;
R.sup.3 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
a cycloalkyl group having from 3 to 6 carbon atoms;
an alkoxy group having from 1 to 6 carbon atoms, said alkoxy group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
an alkenyl group having from 2 to 6 carbon atoms, said alkenyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
an alkynyl group having from 2 to 6 carbon atoms, said alkynyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
a halogen atom;
a nitro group; or
a group of formula --COR.sup.8, wherein R.sup.8 represents a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms, a cycloalkyl group having from 3 to 6 carbon atoms or an alkoxy group having from 1 to 6 carbon atoms;
R.sup.4 and R.sup.5 are the same or different and each represents a hydrogen atom or an alkyl group having from 1 to 6 carbon atoms;
R.sup.6 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
a cycloalkyl group having from 3 to 6 carbon atoms;
an alkoxy group having from 1 to 6 carbon atoms, said alkoxy group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
an alkenyl group having from 2 to 6 carbon atoms, said alkenyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
an alkynyl group having from 2 to 6 carbon atoms, said alkynyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
a halogen atom;
a nitro group; or
a group of formula --COR.sup.8, wherein R.sup.8 represents a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms, a cycloalkyl group having from 3 to 6 carbon atoms or an alkoxy group having from 1 to 6 carbon atoms;
A represents an oxygen atom or a sulfur atom;
X represents an oxygen atom or a sulfur atom;
Y represents a group selected from the group consisting of the groups of formulae --CO--, --COO--, --CH.sub.2 O--, --CH.sub.2 S--, --CH.sub.2 CH.sub.2 O--, --CH.sub.2 CH.sub.2 S --, --CH.sub.2 CO--, --CH.sub.2 COO--, --CH(Me)COO--, --CH.sub.2 CH.sub.2 CO--, --CH.sub.2 OCO--, CH.sub.2 OCOO-- and --CH.sub.2 CH.sub.2 OCO--;
R.sup.7 represents:
an alkyl group having from 1 to 6 carbon atoms, said alkyl group being unsubstituted or being substituted by an alkoxy group having from 1 to 6 carbon atoms, an alkylthio group having from 1 to 6 carbon atoms or by from 1 to 4 halogen atoms;
a cycloalkyl group having from 3 to 6 carbon atoms;
an alkenyl group having from 2 to 6 carbon atoms, said alkenyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
an alkynyl group having from 2 to 6 carbon atoms, said alkynyl group being unsubstituted or being substituted by from 1 to 4 halogen atoms;
a carbocyclic aryl group having from 6 to 14 ring carbon atoms, said aryl group being unsubstituted or being substituted by at least one substituent selected from the group consisting of alkyl groups having from 1 to 6 carbon atoms, alkoxy groups having from 1 to 6 carbon atoms and halogen atoms;
an aralkyl group wherein the aryl moiety is a carbocyclic aryl group having from 6 to 10 ring carbon atoms which is unsubstituted or is substituted by from 1 to 4 halogen atoms, and the alkyl moiety has from 1 to 6 carbon atoms; or
a heterocyclic group having from 4 to 10 ring atoms including at least one ring heteroatom selected from the group consisting of oxygen atoms, sulfur atoms and nitrogen atoms, said heterocyclic group being fully unsaturated, partly unsaturated or saturated and being either unsubstituted, substituted by at least one substituent selected from alkyl groups having from 1 to 6 carbon atoms, alkoxy groups having from 1 to 6 carbon atoms and halogen atoms, or fused with a carbocyclic aryl group having from 6 to 10 ring carbon atoms;
Q represents an oxygen atom or a sulfur atom;
m represents an integer from 0 to 4 and, where m is an integer from 2 to 4, each R.sup.6 may be the same or different; and
n represents an integer from 0 to 4 and, where n is an integer from 2 to 4, each R.sup.3 may be the same or different;
(i) reacting a compound of general formula (II): ##STR22## wherein R.sup.3, A and n are as defined above and K represents a group of formula N(R.sup.2)C(.dbd.X)R.sup.1 wherein R.sup.1, X and R.sup.2 are as defined above, a nitro group or an amino group, with a group of formula (III): ##STR23## wherein R.sup.4, R.sup.5, R.sup.6, Q and m are as defined above and L is a leaving group, to give a compound of formula (Ia), (VIa) or (VIIa): ##STR24## wherein R.sup.3, A, R.sup.4, R.sup.5, R.sup.6, Q, m and n are as defined above and K is as shown;
(ii) where the compound produced in step (i) above is a compound of formula (VIa), wherein K represents a nitro group, reacting said compound with a reducing agent to give a compound of formula (VIIa) wherein K is an amino group;
(iii) where the compound is a compound of formula (VIIa), produced in steps (i) or (ii) above, reacting said compound with a group of formula R.sup.1 C(.dbd.X)L.sup.2 wherein R.sup.1 and X are as defined above and L.sup.2 represents a leaving group, to give a compound of formula (Ia'): ##STR25## wherein R.sup.1, X, R.sup.3, A, R.sup.4, R.sup.5, R.sup.6, Q, m and n are as defined above;
(iv) optionally, reacting said compound of formula (Ia) or (Ia') with a compound of formula R.sup.2a L.sup.3, wherein R.sup.2a represents any of the groups represented by R.sup.2, as defined above, other than a hydrogen atom and L.sup.3 represents a leaving group, to give a compound of formula (Ib'): ##STR26## wherein R.sup.1, R.sup.2a, X, R.sup.3, A, R.sup.4, R.sup.5, R.sup.6, Q, m and n are as defined above;
(v) optionally reacting said compound of formula (Ib') with a suitable reagent to give a compound of formula (Ic'): ##STR27## in which the group of formula R.sup.2a in the compound of formula (Ib') is converted to a group of formula R.sup.2c, wherein R.sup.2c is a different group falling within the definition of the group R.sup.2, and
(vi) optionally, if desired, salifying the resulting compound of formula (I) to give the addition salt thereof.
Referenced Cited
U.S. Patent Documents
4193787 March 18, 1980 Baker
4423237 December 27, 1983 Baker
4500340 February 19, 1985 Becker et al.
4594425 June 10, 1986 Musser et al.
5436267 July 25, 1995 Komyoji et al.
Foreign Patent Documents
081 141 June 1983 EPX
Other references
  • Chemical Abstracts, vol. 99, No. 23, 5 Dec. 1983, Columbus, Ohio, Abstract No. 194949d, p. 754 of JP 58 052280 A (Nissan Chemical Industries, Ltd.) 28 Mar. 1983. Chemical Abstracts, vol. 101, No. 9, 27 Aug. 1984, Columbus, Ohio, Abstract No. 72462d, p. 618, of JP 59 027878 A (Nissan Chemical Industries, Ltd.) 14 Feb. 1984.
Patent History
Patent number: 5736487
Type: Grant
Filed: Mar 7, 1997
Date of Patent: Apr 7, 1998
Assignee: Sankyo Company, Limited (Tokyo)
Inventors: Soji Sugai (Ohtsu), Hiroyuki Komai (Ohmihachiman), Noriaki Kudo (Shiga-ken), Kazuo Sato (Hikone), Toyokuni Honma (Shiga-ken), Junji Kadotani (Shiga-ken), Kiyoshi Koi (Moriyama), Mitsuru Ito (Shiga-ken)
Primary Examiner: Fiona T. Powers
Law Firm: Frishauf, Holtz, Goodman, Langer & Chick, P.C.
Application Number: 8/813,174